4-Hydroxy-1-oxyl-2,2,6,6-tetramethylpiperidine and 4-oxo-1-oxyl-2,2,6,6-tetramethylpiperidine are reported to have been used to trap carbon centered radicals formed from methanol, ethanol, isopropanol and sec-butanol by S. Nigam et al., J. Chem. Soc., Trans. Faraday Soc. 1, 1976, 72, 2324 and by K.-D. Asmus et al., Int. J. Radiat. Biol., 1976, 29, 211.
U.S. Pat. No. 5,627,248 and European Patent Application No. 135,280 A2 describe, respectively, difunctional and monofunctional living free radical polymerization initiators, some of which contain hindered amine ethers substituted by hydroxy groups. These compounds differ substantially in structure and performance from the instant compounds.
European Patent Application No. 427,672 A1 and U.S. Pat. No. 4,972,009 mention, but do not exemplify, respectively, hydroxylamine and nitrone structures, some of which contain C.sub.1 -C.sub.4 hydroxyalkoxy substituted 2,2,6,6-tetramethylpiperidine derivatives. Such structures are outside the scope of the instant invention.
U.S. Pat. No. 5,204,473 describes N-hydrocarbyloxy hindered amine derivatives that are prepared exclusively from organic compounds containing only carbon and hydrogen atoms. Such compounds are structurally quite different from the instant compounds.
U.S. Pat. No. 5,004,770 describes hindered amine compounds which are substituted on the N-atom by alkoxy moieties which alkoxy groups are themselves unsubstituted. These compounds are especially useful in polymers including polybutadiene, polystyrene, ABS, polyacetal, polyamide, polyester, polyurethane and polycaronate.
U.S. Pat. No. 5,096,950 also describes hindered amine compounds which are substituted on the N-atom by alkoxy moieties which alkoxy groups are themselves unsubstituted. These compounds are found to be useful in polyolefins.
The instant compounds are N-alkoxy substituted derivatives of 2,2,6,6-tetraalkylpiperidines where the alkoxy group is substituted by one to three hydroxy moieties. The instant compounds also comprise N-alkoxy bridged derivatives of the 2,2,6,6-tetraalkylpiperidines where the alkoxy moiety, which is substituted by one to three hydroxy groups, is shared by two hindered amine molecules. The free hydroxy moieties of these compounds may be reacted with carboxylic acids, acid chlorides or esters to form simple esters or polyesters, or with isocyanates to form urethanes or polyurethanes.
The instant compounds, because of their low bascity which is shared by the simple unsubstituted N-alkoxy compounds cited in the two patents mentioned above, are of particular value in the stabilization of polyolefins and automotive coating compositions where the activity of the more basic hindered amine stabilizes is significantly reduced because of interaction with the polymer substrate or acid catalytic system needed for curing such substrate.
Examples of polyolefin compositions in which the instant compounds are effective include flame retardant polyolefins where acidic residues from the decomposition of the halogenated flame retardants deactivate hindered amines not having the N--OR group, greenhouse films and agricultural mulch films where acidic residues from pesticides interfere with the activity of "normal" hindered amine stabilizers, and in thermoplastic polyolefins where pigment interactions with basic hindered amine stabilizers interfere with painting the substrate surfaces. Examples of coating compositions in which the instant compounds are effective include melamine crosslinked thermoset acrylic resins, which are cured using strong acids that interact with basic hindered amine stabilizers. The instant compounds are also effective in acrylic alkyd or polyester resins with isocyanate crosslinking agents, and in epoxy resins with carboxylic acid, anhydride, or amine crosslinking agents.
While the unsubstituted N--OR compounds described in U.S. Pat. Nos. 5,004,770 and 5,096,950 also perform well in the compositions described in the paragraph above, the instant compounds differ significantly in both structure and in performance from the prior art compounds by virtue of the presence of the one to three free hydroxy groups present on the N-alkoxy moiety. These hydroxyl groups in the instant compounds provide said compounds with superior antistatic properties, compatibility in more polar environments such as polyurethane based and in water-borne automotive coating systems, and in stabilizing painted automotive thermoplastic olefin structures.
The instant compounds are particularly suited for
(a) providing superior compatibility in polycarbonates and polycarbonate/ABS blends compared to the N--OE prior art compounds; and PA1 (b) providing superior compatibility in polyesters and polyamides compared to the prior art N--OE compounds. PA1 1. Novel compounds having on the 1-position of the hindered amine a moiety --O--E--OH where the OH group provides important properties; and PA1 2. Compositions stabilized by the novel compounds described above. PA1 G.sub.1 and G.sub.2 are independently alkyl of 1 to 4 carbon atoms, or G.sub.1 and G.sub.2 together are pentamethylene; preferably G.sub.1 and G.sub.2 are each methyl; PA1 E is a straight or branched chain alkylene of 1 to 18 carbon atoms, cycloalkylene of 5 to 18 carbon atoms, cycloalkenylene of 5 to 18 carbon atoms, a straight or branched chain alkylene of 1 to 4 carbon atoms substituted by phenyl or by phenyl substituted by one or two alkyl groups of 1 to 4 carbon atoms; PA1 b is 1, 2 or 3 with the proviso that b cannot exceed the number of carbon atoms in E or L, and when b is 2 or 3, each hydroxyl group is attached to a different carbon atom of E or L; the two hindered amine groups are generally, but not always, attached to two different carbon atoms of L; PA1 in each of the formulas (1) to (15) PA1 m is 0 or 1; PA1 R.sub.1 is hydrogen, hydroxyl or hydroxymethyl; PA1 R.sub.2 is hydrogen, alkyl of 1 to 12 carbon atoms or alkenyl of 2 to 12 carbon atoms; PA1 n is 1 to 4; PA1 when n is 1, PA1 R.sub.3 is alkyl of 1 to 18 carbon atoms, alkoxycarbonylalkylenecarbonyl of 4 to 18 carbon atoms, alkenyl of 2 to 18 carbon atoms, glycidyl, 2,3-dihydroxypropyl, 2-hydroxy or 2-(hydroxymethyl) substituted alkyl of 3 to 12 carbon atoms which alkyl is interrupted by oxygen, an acyl radical of an aliphatic or unsaturated aliphatic carboxylic or carbamic acid containing 2 to 18 carbon atoms, an acyl radical of a cycloaliphatic carboxylic or carbamic acid containing 7 to 12 carbon atoms, or acyl radical of an aromatic acid containing 7 to 15 carbon atoms; PA1 when n is 2, PA1 R.sub.3 is alkylene of 2 to 18 carbon atoms, a divalent acyl radical of an aliphatic or unsaturated aliphatic dicarboxylic or dicarbamic acid containing 2 to 18 carbon atoms, a divalent acyl radical of a cycloaliphatic dicarboxylic or dicarbamic acid containing 7 to 12 carbon atoms, or a divalent acyl radical of an aromatic dicarboxylic acid containing 8 to 15 carbon atoms; PA1 when n is 3, PA1 R.sub.3 is a trivalent acyl radical of an aliphatic or unsaturated aliphatic tricarboxylic acid containing 6 to 18 carbon atoms, or a trivalent acyl radical of an aromatic tricarboxylic acid containing 9 to 15 carbon atoms; PA1 when n is 4, PA1 R.sub.3 is a tetravalent acyl radical of an aliphatic or unsaturated aliphatic tetracarboxylic acid, especially 1,2,3,4-butanetetracarboxylic acid, 1,2,3,4-but-2-enetetracarboxylic acid, 1,2,3,5-pentanetetracarboxylic acid and 1,2,4,5-pentanetetracarboxylic acid, or R.sub.3 is a tetravalent acyl radical of an aromatic tetracarboxylic acid containing 10 to 18 carbon atoms; PA1 p is 1 to 3, PA1 R.sub.4 is hydrogen, alkyl of 1 to 18 carbon atoms or acyl of 2 to 6 carbon atoms; PA1 when p is 1, PA1 R.sub.5 is hydrogen, alkyl of 1 to 18 carbon atoms, an acyl radical of an aliphatic or unsaturated aliphatic carboxylic or carbamic acid containing 2 to 18 carbon atoms, an acyl radical of a cycloaliphatic carboxylic or carbamic acid containing 7 to 12 carbon atoms, an acyl radical of an aromatic carboxylic acid containing 7 to 15 carbon atoms, or R.sub.4 and R.sub.5 together are --(CH.sub.2).sub.5 CO--, phthaloyl or a divalent acyl radical of maleic acid; PA1 when p is 2, PA1 R.sub.5 is alkylene of 2 to 12 carbon atoms, a divalent acyl radical of an aliphatic or unsaturated aliphatic dicarboxylic or dicarbamic add containing 2 to 18 carbon atoms, a divalent acyl radical of a cycloaliphatic dicarboxylic or dicarbamic acid containing 7 to 12 carbon atoms, or a divalent acyl radical of an aromatic dicarboxylic acid containing 8 to 15 carbon atoms; PA1 when p is 3, PA1 R.sub.5 is a trivalent acyl radical of an aliphatic or unsaturated aliphatic tricarboxylic acid containing 6 to 18 carbon atoms, or a trivalent acyl radical of an aromatic tricarboxylic acid containing 9 to 15 carbon atoms; PA1 when n is 1, PA1 R.sub.6 is alkoxy of 1 to 18 carbon atoms, alkenyloxy of 2 to 18 carbon atoms, --NHalkyl of 1 to 18 carbon atoms or --N(alkyl).sub.2 of 2 to 36 carbon atoms, PA1 when n is 2, PA1 R.sub.6 is alkylenedioxy of 2 to 18 carbon atoms, alkenylenedioxy of 2 to 18 carbon atoms, --NH-alkylene-NH-- of 2 to 18 carbon atoms or --N(alkyl)-alkylene-N(alkyl)- of 2 to 18 carbon atoms, or R.sub.6 is 4-methyl-1,3-phenylenediamino, PA1 when n is 3, PA1 R.sub.6 is a trivalent alkoxy radical of a saturated or unsaturated aliphatic triol containing 3 to 18 carbon atoms, PA1 when n is 4, PA1 R.sub.6 is a tetravalent alkoxy radical of a saturated or unsaturated aliphatic tetraol containing 4 to 18 carbon atoms, PA1 R.sub.7 and R.sub.8 are independently chlorine, alkoxy of 1 to 18 carbon atoms, --O--T.sub.1, amino substituted by 2-hydroxyethyl, --NH(alkyl) of 1 to 18 carbon atoms, --N(alkyl)T.sub.1 with alkyl of 1 to 18 carbon atoms, or --N(alkyl).sub.2 of 2 to 36 carbon atoms, PA1 R.sub.9 is a divalent oxygen atom, or R.sub.9 is a divalent nitrogen atom substituted by either hydrogen, alkyl of 1 to 12 carbon atoms or T.sub.1 ##STR5## PA1 R.sub.10 is hydrogen or methyl, PA1 q is 2 to 8, PA1 R.sub.11 and R.sub.12 are independently hydrogen or the group T.sub.2 ##STR6## PA1 R.sub.13 is hydrogen, phenyl, straight or branched alkyl of 1 to 12 carbon atoms, alkoxy of 1 to 12 carbon atoms, straight or branched alkyl of 1 to 4 carbon atoms substituted by phenyl, cycloalkyl of 5 to 8 carbon atoms, cycloalkenyl of 5 to 8 carbon atoms, alkenyl of 2 to 12 carbon atoms, glycidyl, allyloxy, straight or branched hydroxyalkyl of 1 to 4 carbon atoms, or silyl or silyloxy substituted three times independently by hydrogen, by phenyl, by alkyl of 1 to 4 carbon atoms or by alkoxy of 1 to 4 carbon atoms; PA1 R.sub.14 is hydrogen or silyl substituted three times independently by hydrogen, by phenyl, by alkyl of 1 to 4 carbon atoms or by alkoxy of 1 to 4 carbon atoms; PA1 d is 0 or 1; PA1 h is 0 to 4; PA1 k is 0 to 5; PA1 x is 3 to 6; PA1 y is 1 to 10; PA1 z is an integer such that the compound has a molecular weight of 1000 to 4000 amu, PA1 R.sub.15 is morpholino, piperidino, 1-piperizinyl, alkylamino of 1 to 8 carbon atoms, especially branched alkylamino of 3 to 8 carbon atoms such as tert-octylamino, --N(alkyl)T.sub.1 with alkyl of 1 to 8 carbon atoms, or --N(alkyl).sub.2 of 2 to 16 carbon atoms, PA1 R.sub.16 is hydrogen, acyl of 2 to 4 carbon atoms, carbamoyl substituted by alkyl of 1 to 4 carbon atoms, s-triazinyl substituted once by chlorine and once by R.sub.15, or s-triazinyl substituted twice by R.sub.15 with the condition that the two R.sub.15 substituents may be different; PA1 R.sub.17 is chlorine, amino substituted by alkyl of 1 to 8 carbon atoms or by T.sub.1, --N(alkyl)T.sub.1 with alkyl of 1 to 8 carbon atoms, --N(alkyl).sub.2 of 2 to 16 carbon atoms, or the group T.sub.3 ##STR7## PA1 R.sub.18 is hydrogen, acyl of 2 to 4 carbon atoms, carbamoyl substituted by alkyl of 1 to 4 carbon atoms, s-triazinyl substituted twice by --N(alkyl).sub.2 of 2 to 16 carbon atoms or s-triazinyl substituted twice by --N(alkyl)T.sub.1 with alkyl of 1 to 8 carbon atoms; PA1 L is straight or branched chain alkylene of 1 to 18 carbon atoms, cycloalkylene of 5 to 8 carbon atoms, cycloalkenylene of 5 to 8 carbon atoms, alkenylene of 3 to 18 carbon atoms, a straight or branched chain alkylene of 1 to 4 carbon atoms substituted by phenyl or by phenyl substituted by one or two alkyl of 1 to 4 carbon atoms, PA1 in formulas (16) to (28), R.sub.1, R.sub.2, R.sub.7, R.sub.8, R.sub.9, R.sub.10, R.sub.13, R.sub.14, d, h, k, m, q, and T.sub.1 have the same meanings as in formulas (1) to (15); PA1 R.sub.19 is hydrogen, alkyl of 1 to 18 carbon atoms, alkenyl of 2 to 18 carbon atoms, glycidyl, 2,3-dihydroxypropyl, 2-hydroxy or 2-(hydroxymethyl substituted alkyl of 3 to 12 carbon atoms which alkyl is interrupted by oxygen, an acyl radical of an aliphatic or unsaturated aliphatic carboxylic or carbamic acid containing 2 to 18 carbon atoms, an acyl radical of a cycloaliphatic carboxylic or carbamic acid containing 7 to 12 carbon atoms, or acyl radical of an aromatic acid containing 7 to 15 carbon atoms; PA1 R.sub.20 is alkylene of 2 to 18 carbon atoms, a divalent acyl radical of an aliphatic or unsaturated aliphatic dicarboxylic or dicarbamic acid containing 2 to 18 carbon atoms, a divalent acyl radical of a cycloaliphatic dicarboxylic or dicarbamic acid containing 7 to 12 carbon atoms, or a divalent acyl radical of an aromatic dicarboxylic acid containing 8 to 15 carbon atoms; PA1 R.sub.21, is hydrogen, alkyl of 1 to 18 carbon atoms or acyl of 2 to 6 carbon atoms; PA1 R.sub.22 is hydrogen, alkyl of 1 to 18 carbon atoms, an acyl radical of an aliphatic or unsaturated aliphatic carboxylic or carbamic acid containing 2 to 18 carbon atoms, an acyl radical of a cycloaliphatic carboxylic or carbamic acid containing 7 to 12 carbon atoms, an acyl radical of an aromatic carboxylic acid containing 7 to 15 carbon atoms, or R.sub.4 and R.sub.5 together are --(CH.sub.2).sub.5 CO--, phthaloyl or a divalent acyl radical of maleic acid; PA1 R.sub.23 is hydrogen, alkyl of 1 to 4 carbon atoms or acyl of 2 to 6 carbon atoms; PA1 R.sub.24 is alkylene of 2 to 18 carbon atoms, a divalent acyl radical of an aliphatic or unsaturated aliphatic dicarboxylic or dicarbamic acid containing 2 to 18 carbon atoms, a divalent acyl radical of a cycloaliphatic dicarboxylic or dicarbamic acid containing 7 to 12 carbon atoms, or a divalent acyl radical of an aromatic dicarboxylic acid containing 8 to 15 carbon atoms; PA1 R.sub.25 is alkoxy of 1 to 18 carbon atoms, alkenyloxy of 2 to 18 carbon atoms, --NHalkyl of 1 to 18 carbon atoms or --N(alkyl).sub.2 of 2 to 36 carbon atoms, PA1 R.sub.26 is alkylenedioxy of 2 to 18 carbon atoms, alkenylenedioxy of 2 to 18 carbon atoms, --NH-alkylene-NH-- of 2 to 18 carbon atoms or --N(alkyl)-alkylene-N(alkyl)- of 3 to 18 carbon atoms, PA1 in formulas (29) and (30), G is a carbon centered diradical derived from a primary, secondary or tertiary alcohol G--OH, where PA1 z is as defined above, and PA1 G is straight or branched chain alkylene of 1 to 18 carbon atoms, cycloalkylene of 5 to 8 carbon atoms, cycloalkenylene of 5 to 8 carbon atoms, alkenylene of 3 to 18 carbon atoms, a straight or branched chain alkylene of 1 to 4 carbon atoms substituted by phenyl or by phenyl substituted by one or two alkyl of 1 to 4 carbon atoms, with the proviso that in formula (29) successive hindered amine moieties can be oriented in either a head to head or head to tail fashion; PA1 T.sub.4 is hydrogen or ##STR8## PA1 R.sub.27 is a straight or branched chain alkylene of 1 to 18 carbon atoms, cycloalkylene or cycdoalkenylene of 5 to 8 carbon atoms, phenylene or --NH-alkylene-NH-- of 2 to 18 carbon atoms including 5-amino-1-aminomethyl-1,3,3-trimethylcycdohexane and --NH-xylylene-NH--; PA1 R.sub.28 is alkyl of 1 to 4 carbon atoms; ##STR9## PA1 R.sub.29 is a straight or branched chain alkyl or --NH-alkyl of 1 to 18 carbon atoms or --NH-cycloalkyl of 5 to 8 carbon atoms; and PA1 with the further proviso that in formulas (1) and (2), when b is 1, E is not methyl, ethyl, 2-propyl or 2-methyl-2-propyl. PA1 a) radical polymerisation (normally under high pressure and at elevated temperature). PA1 b) catalytic polymersation using a catalyst that normally contains one or more than one metal of groups IVb, Vb, VIb or VIII of the Periodic Table. These metals usually have one or more than one ligand, typically oxides, halides, alcoholates, esters, ethers, amines, alkyls, alkenyis and/or aryls that may be either .pi.- or .sigma.-coordinated. These metal complexes may be in the free form or fixed on substrates, typically on activated magnesium chloride, titanium(ll) chloride, alumina or silicon oxide. These catalysts may be soluble or insoluble in the polymerisation medium. The catalysts can be used by themselves in the polymerisation or further activators may be used, typically metal alkyls, metal hydrides, metal alkyl halides, metal alkyl oxides or metal alkyloxanes, said metals being elements of groups Ia, IIa and/or IIIa of the Periodic Table. The activators may be modified conveniently with further ester, ether, amine or silyl ether groups. These catalyst systems are usually termed Phillips, Standard Oil Indiana, Ziegler (-Natta), TNZ (DuPont), metallocene or single site catalysts (SSC). PA1 2,6-di-tert-butyl-4-methylphenol PA1 2-tert-butyl-4,6-dimethylphenol PA1 2,6-di-tert-butyl-4-ethylphenol PA1 2,6-di-tert-butyl-4-n-butylphenol PA1 2,6-di-tert-butyl-4-i-butylphenol PA1 2,6-di-cyclopentyl-4-methylphenol PA1 2-(.alpha.-methylcyclohexyl)-4,6-dimethyephenol PA1 2,6-di-octadecyl-4-methylphenol PA1 2,4,6-tri-cyclohexylphenol PA1 2,6-di-tert-butyl-4-methoxymethylphenol PA1 2,6-di-tert-butyl-4-methoxyphenol PA1 2,5-di-tert-butyl-hydroquinone PA1 2,5-di-tert-amyl-hydroquinone PA1 2,6-diphenyl-4-octadecyloxyphenol PA1 2,2'-thio-bis-(6-tert-butyl-4-methylphenol) PA1 2,2'-thio-bis-(4-octylphenol) PA1 4,4'-thio-bis-(6-tert-butyl-3-methylphenol) PA1 4,4'-thio-bis-(6-tert-butyl-2-methylphenol) PA1 2,2'-methylene-bis-(6-tert-butyl-4-methylphenol) PA1 2,2'-methylene-bis-(6-tert-butyl-4-ethylphenol) PA1 2,2'-methylene-bis-[4-methyl-6-(.alpha.-methylcyclohexyl)-phenol] PA1 2,2'-methylene-bis-(4-methyl-6-cyclohexylphenol) PA1 2,2'-methylene-bis-(6-nonyl-4-methylphenol) PA1 2,2'-methylene-bis-[6-(.alpha.-methylbenzyl)-4-nonylphenol] PA1 2,2'-methylene-bis-[6-(.alpha.,.alpha.-dimethylbenzyl)-4-nonylphenol] PA1 2,2'-methylene-bis-(4,6-di-tert-butylphenol) PA1 2,2'-ethylidene-bis-(4,6-di-tert-butylphenol) PA1 2,2'-ethylidene-bis-(6-tert-butyl-4-isobutylphenol) PA1 4,4'-methylene-bis-(2,6-di-tert-butylphenol) PA1 4,4'-methylene-bis-(6-tert-butyl-2-methylphenol) PA1 1,1-bis-(5-tert-butyl-4-hydroxy-2-methylphenyl)-butane PA1 2,6-di-(3-tert-butyl-5-methyl-2-hydroxybenzyl-4-methylphenol PA1 1,1,3-tris-(5-tert-butyl-4-hydroxy-2-methylphenyl)-butane PA1 1,1-bis-(5-tert-butyl-4-hydroxy-2-methylphenyl)-3-n-dodecylmercaptobutane PA1 ethyleneglycol bis-[3,3-bis-(3'-tert-butyl-4'-hydroxyphenyl)-butyrate] PA1 di-(3-tert-butyl-4-hydroxy-5-methylphenyl)-dicyclopentadiene PA1 di-[2-(3'-tert-butyl-2'-hydroxy-5'-methyl-benzyl)-6-tert-butyl-4-methylphen yl]terephthalate. PA1 1,3,5-tri-(3,5-di-tert-butyl-4-hydroxybenzyl)-2,4,6-trimethylbenzene PA1 di-(3,5-di-tert-butyl-4-hydroxybenzyl) sulfide PA1 3,5-di-tert-butyl-4-hydroxybenzyl-mercapto-acetic acid isooctyl ester PA1 bis-(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl)dithiol terephthalate PA1 1,3,5-tris-(3,5-di-tert-butyl-4-hydroxybenzyl) isocyanurate PA1 1,3,5-tris-(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl) isocyanurate PA1 3,5-di-tert-butyl-4-hydroxybenzyl-phosphoric acid dioctadecyl ester PA1 3,5-di-tert-butyl-4-hydroxybenzyl-phosphoric acid monoethyl ester, calcium-salt PA1 4-hydroxy-lauric acid anilide PA1 4-hydroxy-stearic acid anilide PA1 2,4-bis-octylmercapto-6-(3,5-tert-butyl-4-hydroxyanilino)-s-triazine PA1 octyl-N-(3,5-di-tert-butyl-4-hydroxyphenyl)-carbamate PA1 N,N'-di-(3,5-di-tert-butyl-4-hydroxyphenylpropionyl)-hexamethylenediamine PA1 N,N'-di-(3,5-di-tert-butyl-4-hydroxyphenylpropionyl)-trimethylenediamine PA1 N,N'-di-(3,5-di-tert-butyl-4-hydroxyphenylpropionyl)-hydrazine PA1 diphenylamine, N-phenyl-1-naphthylamine, N-(4-tert-octylphenyl)-1-naphthylamine, 4,4'-di-tert-octyl-diphenylamine, reaction product of N-phenylbenzylamine and 2,4,4-trimethylpentene, reaction product of diphenylamine and 2,4,4-trimethylpentene, reaction product of N-phenyl-1-naphthylamine and 2,4,4-trimethylpentene. PA1 2-(2-hydroxy-3,5-di-tert-amylphenyl)-2H-benzotriazole; PA1 2-[2-hydroxy-3,5-di(.alpha.,.alpha.-dimethylbenzyl)phenyl]-2H-benzothiazole ; PA1 2-[2-hydroxy-3-(.alpha.,.alpha.-dimethylbenzyl)-5-tert-octylphenyl]-2H-benz otriazole; PA1 2-{2-hydroxy-3-tert-butyl-5-[2-(omega-hydroxy-octa(ethyleneoxy)carbonyl)eth yl]phenyl}-2H-benzotriazole; and PA1 2-{2-hydroxy-3-tert-butyl-5-[2-(octyloxy)carbonyl)ethyl]phenyl}-2H-benzotri azole. PA1 (a) 5-trifluoromethyl-2-(2-hydroxy-3-.alpha.-cumyl-5-tert-octylphenyl)-2H-benz otriazole; PA1 (b) 5-trifluoromethyl-2-(2-hydroxy-5-tert-octylphenyl)-2H-benzotriazole; PA1 (c) 5-trifluoromethyl-2-(2-hydroxy-3,5-di-tert-octylphenyl)-2H-benzotriazole; PA1 (d) 2,2'-methylene-bis[6-(5-trifluoromethyl-2H-benzotriazol-2-yl)-4-tert-octyl phenol]; PA1 (e) methylene-2-[4-tert-octyl-6-(2H-benzotriazol-2-yl)phenol]2'-[4-tert-octyl- 6-(5-triflouromethyl-2H-benzotriazol-2-yl)phenol]; PA1 (f) 3-(5-trifluoromethyl-2H-benzotriazol-2-yl)-5-tert-butyl-4-hydroxyhydrocinn amate acid; PA1 (g) methyl 3-(5-trifluoromethyl-2H-benzotriazol-2-yl)tert-butyl-4-hydroxyhydrocinnama te; PA1 (h) isooctyl 3-(5-trifluoromethyl-2H-benzotriazol-2-yl)-5-tert-butyl-4-hydroxyhydrocinn amate; PA1 (i) 5-trifluoromethyl-2-[2-hydroxy-5-(3-hydroxypropyl)phenyl]-2H-benzotriazole ; PA1 (j) 5-trifluoromethyl-2-[2-hydroxy-5-(3-acryloyloxypropyl)phenyl]-2H-benzotria zole; PA1 (k) 5-trifluoromethyl-2-[2-hydroxy-5-(3-methacryloyloxypropyl)phenyl]-2H-benzo triazole; PA1 (l) 5-trifluoromethyl-2-[2-hydroxy-5-(3-acrylylaminopropyl)phenyl]-2H-benzotri azole; PA1 (m) 5-trifluoromethyl-2-[2-hydroxy-5-(3-methacrylylaminopropyl)phenyl]-2H-benz otriazole; PA1 (n) 5-trifluoromethyl-2-(2-hydroxy-3-.alpha.-cumyl-5-tert-butylphenyl)-2H-benz otriazole; PA1 (o) 5-trifluoromethyl-2-(2-hydroxy-3-.alpha.-cumyl-5-nonylphenyl)-2H-benzotria zole; PA1 (p) 5-trifluoromethyl-2-[2-hydroxy-3-.alpha.-cumyl-5-(2-hydroxyethyl)phenyl]-2 H-benzotriazole; PA1 (q) 5-trifluoromethyl-2-[2-hydroxy-3-.alpha.-cumyl-5-(3-hydroxypropyl)phenyl]- 2H-benzotriazole; PA1 (r) 5-trifluoromethyl-2-(2-hydroxy-3,5-di-tert-amylphenyl)-2H-benzotriazole; PA1 (s) 5-trifluoromethyl-2-(2-hydroxy-3,5-di-tert-butylphenyl)-2H-benzotriazole; PA1 (t) 5-trifluoromethyl-2-(2-hydroxy-3-dodecyl-5-methylphenyl)-2H-benzotriazole; PA1 (u) 5-trifluoromethyl-2-[2-hydroxy-3-tert-butyl-5-(3-hydroxypropyl)phenyl)-2H- benzotriazole; PA1 (v) 5-trifluoromethyl-2-[2-hydroxy-3-tert-butyl-5-(2-hydroxyethyl)phenyl]-2H-b enzotriazole; PA1 (w) 5-trifluoromethyl-2-[2-hydroxy-5-(2-hydroxyethyl)phenyl]-2H-benzotriazole; PA1 (x) 5-trifluoromethyl-2-(2-hydroxy-3,5-di-.alpha.-cumylphenyl)-2H-benzotriazol e; PA1 (y) 5-fluoro-2-(2-hydroxy-3,5-di-.alpha.-cumylphenyl)-2H-benzotriazole; PA1 (z) 5-butylsulfonyl-2-(2-hydroxy-3,5-di-.alpha.-cumylphenyl)-2H-benzotriazole; PA1 (aa) 5-butylsulfonyl-2-(2-hydroxy-3,5-di-tert-butylphenyl)-2H-benzotriazole; PA1 (bb) 5-butylsulfonyl-2-(2-hydroxy-3,5-di-tert-octylphenyl)-2H-benzotriazole; and PA1 (cc) 5-phenylsulfonyl-2-(2-hydroxy-3,5-di-tert-butylphenyl)-2H-benzotriazole. PA1 2,4-bis(2,4-dimethylphenyl)-6-(2-hydroxy-4-octyloxyphenyl)-s-triazine; PA1 2,4-diphenyl-6-(2-hydroxy-4-4-hexyloxyphenyl)-s-triazine; PA1 2,4-bis(2,4-dimethylphenyl)-6-[2-hydroxy-4-(3-do-/ tri-decyloxy-2-hydroxypropoxy)phenyl]-s-triazine; and PA1 2-(2-hydroxyethylamino)-4,6-bis[N-butyl-N-(1-cyclohexyloxy-2,2,6,6-tetramet hylpiperidin-4-yl)amino]-s-triazine.